AU726272B2 - Manufacture of cross-linked amylose useful as an excipient for control release of active compounds - Google Patents

Manufacture of cross-linked amylose useful as an excipient for control release of active compounds Download PDF

Info

Publication number: AU726272B2
Authority: AU; Australia
Prior art keywords: cross; linked; starch; high amylose; amylose starch
Prior art date: 1997-02-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Ceased

Application number

AU59785/98A

Other languages

English (en)

Other versions

AU5978598A (en

Inventor

Francois Carriere

Yves Dumoulin

Andre Ingenito

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Labopharm Barbados Ltd

Labopharm Inc

Paladin Labs Europe Ltd

Original Assignee

Labopharm Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-02-14

Filing date

1998-02-10

Publication date

2000-11-02

1998-02-10 Application filed by Labopharm Inc filed Critical Labopharm Inc

1998-09-08 Publication of AU5978598A publication Critical patent/AU5978598A/en

2000-11-02 Application granted granted Critical

2000-11-02 Publication of AU726272B2 publication Critical patent/AU726272B2/en

2004-09-09 Assigned to LABOPHARM (BARBADOS) LIMITED, LABOPHARM INC., LABOPHARM EUROPE LIMITED reassignment LABOPHARM (BARBADOS) LIMITED Alteration of Name(s) in Register under S187 Assignors: LABOPHARM INC.

2018-02-10 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

229920000856 Amylose Polymers 0.000 title claims abstract description 64
239000000546 pharmaceutical excipient Substances 0.000 title claims abstract description 27
238000004519 manufacturing process Methods 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 title description 3
239000000047 product Substances 0.000 claims abstract description 75
229920001685 Amylomaize Polymers 0.000 claims abstract description 72
229920002472 Starch Polymers 0.000 claims abstract description 46
235000019698 starch Nutrition 0.000 claims abstract description 45
239000008107 starch Substances 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 44
239000002002 slurry Substances 0.000 claims abstract description 35
230000008569 process Effects 0.000 claims abstract description 31
238000007669 thermal treatment Methods 0.000 claims abstract description 29
239000002245 particle Substances 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 16
239000003431 cross linking reagent Substances 0.000 claims abstract description 15
239000006227 byproduct Substances 0.000 claims abstract description 14
239000007787 solid Substances 0.000 claims abstract description 13
239000012429 reaction media Substances 0.000 claims abstract description 11
239000008188 pellet Substances 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 7
239000012736 aqueous medium Substances 0.000 claims abstract description 6
239000002609 medium Substances 0.000 claims abstract description 6
239000003513 alkali Substances 0.000 claims abstract description 5
239000007795 chemical reaction product Substances 0.000 claims abstract description 5
238000013270 controlled release Methods 0.000 claims description 27
238000004132 cross linking Methods 0.000 claims description 16
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 14
238000001694 spray drying Methods 0.000 claims description 13
238000001704 evaporation Methods 0.000 claims description 10
230000008020 evaporation Effects 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
239000006185 dispersion Substances 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 7
230000000930 thermomechanical effect Effects 0.000 claims description 7
238000000108 ultra-filtration Methods 0.000 claims description 7
238000001035 drying Methods 0.000 claims description 6
238000005550 wet granulation Methods 0.000 claims description 6
238000004108 freeze drying Methods 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
UGTZMIPZNRIWHX-UHFFFAOYSA-K sodium trimetaphosphate Chemical compound [Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 UGTZMIPZNRIWHX-UHFFFAOYSA-K 0.000 claims description 4
OMFRWBLRAMQSDM-UHFFFAOYSA-N 6-acetyloxy-6-oxohexanoic acid Chemical compound CC(=O)OC(=O)CCCCC(O)=O OMFRWBLRAMQSDM-UHFFFAOYSA-N 0.000 claims description 2
230000003472 neutralizing effect Effects 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
238000010298 pulverizing process Methods 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000003826 tablet Substances 0.000 description 51
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000007921 spray Substances 0.000 description 23
239000003814 drug Substances 0.000 description 22
229940079593 drug Drugs 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 17
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 14
238000000338 in vitro Methods 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000000843 powder Substances 0.000 description 13
238000011026 diafiltration Methods 0.000 description 12
229920000881 Modified starch Polymers 0.000 description 11
238000007922 dissolution test Methods 0.000 description 11
239000008187 granular material Substances 0.000 description 10
239000012528 membrane Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000012530 fluid Substances 0.000 description 9
235000019426 modified starch Nutrition 0.000 description 8
238000012360 testing method Methods 0.000 description 8
229960005489 paracetamol Drugs 0.000 description 7
239000007884 disintegrant Substances 0.000 description 6
238000009826 distribution Methods 0.000 description 6
238000011156 evaluation Methods 0.000 description 6
230000036571 hydration Effects 0.000 description 6
238000006703 hydration reaction Methods 0.000 description 6
238000013268 sustained release Methods 0.000 description 6
239000012730 sustained-release form Substances 0.000 description 6
229920000945 Amylopectin Polymers 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
238000007907 direct compression Methods 0.000 description 5
238000004090 dissolution Methods 0.000 description 5
238000005469 granulation Methods 0.000 description 5
230000003179 granulation Effects 0.000 description 5
230000000877 morphologic effect Effects 0.000 description 5
239000012738 dissolution medium Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000011148 porous material Substances 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
238000010998 test method Methods 0.000 description 4
230000009466 transformation Effects 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
238000005384 cross polarization magic-angle spinning Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000945 filler Substances 0.000 description 3
235000013305 food Nutrition 0.000 description 3
238000009472 formulation Methods 0.000 description 3
230000036541 health Effects 0.000 description 3
229920002521 macromolecule Polymers 0.000 description 3
229920002492 poly(sulfone) Polymers 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
239000004382 Amylase Substances 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
238000013019 agitation Methods 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
AZSFNUJOCKMOGB-UHFFFAOYSA-K cyclotriphosphate(3-) Chemical compound [O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 AZSFNUJOCKMOGB-UHFFFAOYSA-K 0.000 description 2
238000011161 development Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000012377 drug delivery Methods 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
230000003628 erosive effect Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000013505 freshwater Substances 0.000 description 2
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000002386 leaching Methods 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
108010082495 Dietary Plant Proteins Proteins 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
238000005004 MAS NMR spectroscopy Methods 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000005388 cross polarization Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000011978 dissolution method Methods 0.000 description 1
238000009509 drug development Methods 0.000 description 1
238000000909 electrodialysis Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000005243 fluidization Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
239000007863 gel particle Substances 0.000 description 1
235000021474 generally recognized As safe (food) Nutrition 0.000 description 1
235000021472 generally recognized as safe Nutrition 0.000 description 1
235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
210000002429 large intestine Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
239000012466 permeate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000020978 protein processing Effects 0.000 description 1
238000007670 refining Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007939 sustained release tablet Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
230000002522 swelling effect Effects 0.000 description 1
239000004753 textile Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/003—Crosslinking of starch
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B33/00—Preparation of derivatives of amylose

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Biochemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compounds Of Unknown Constitution (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Saccharide Compounds (AREA)

AU59785/98A 1997-02-14 1998-02-10 Manufacture of cross-linked amylose useful as an excipient for control release of active compounds Ceased AU726272B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/800518		1997-02-14
US08/800,518 US5807575A (en)	1997-02-14	1997-02-14	Manufacture of cross-linked amylose useful as a excipient for control release of active compounds
PCT/CA1998/000106 WO1998035992A1 (en)	1997-02-14	1998-02-10	Manufacture of cross-linked amylose useful as an excipient for control release of active compounds

Publications (2)

Publication Number	Publication Date
AU5978598A AU5978598A (en)	1998-09-08
AU726272B2 true AU726272B2 (en)	2000-11-02

Family

ID=25178603

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU59785/98A Ceased AU726272B2 (en)	1997-02-14	1998-02-10	Manufacture of cross-linked amylose useful as an excipient for control release of active compounds

Country Status (12)

Country	Link
US (1)	US5807575A (de)
EP (1)	EP0960131B1 (de)
AT (1)	ATE212040T1 (de)
AU (1)	AU726272B2 (de)
CA (1)	CA2280534C (de)
DE (1)	DE69803159T2 (de)
DK (1)	DK0960131T3 (de)
ES (1)	ES2171008T3 (de)
IL (1)	IL131369A (de)
NZ (1)	NZ337171A (de)
PT (1)	PT960131E (de)
WO (1)	WO1998035992A1 (de)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7153845B2 (en) *	1998-08-25	2006-12-26	Columbia Laboratories, Inc.	Bioadhesive progressive hydration tablets
US8765177B2 (en) *	1997-09-12	2014-07-01	Columbia Laboratories, Inc.	Bioadhesive progressive hydration tablets
US6624200B2 (en)	1998-08-25	2003-09-23	Columbia Laboratories, Inc.	Bioadhesive progressive hydration tablets
US6248358B1 (en)	1998-08-25	2001-06-19	Columbia Laboratories, Inc.	Bioadhesive progressive hydration tablets and methods of making and using the same
US6284273B1 (en) *	1998-02-24	2001-09-04	Vincent Lenaerts	Cross-linked high amylose starch resistant to amylase as a matrix for the slow release of biologically active compounds
GB9924351D0 (en) *	1999-10-14	1999-12-15	Brennan Frank	Immunomodulation methods and compositions
US6607748B1 (en) *	2000-06-29	2003-08-19	Vincent Lenaerts	Cross-linked high amylose starch for use in controlled-release pharmaceutical formulations and processes for its manufacture
WO2002045695A2 (en)	2000-12-05	2002-06-13	Alexander Macgregor	Hydrostatic delivery system for controlled delivery of agent
CA2423712A1 (en)	2003-03-26	2004-09-26	Nicolas Nourry	Crosslinked amylopectin by reactive extrusion and its use as an absorbent or superabsorbent material
TWI319713B (en) *	2002-10-25	2010-01-21		Sustained-release tramadol formulations with 24-hour efficacy
US8487002B2 (en) *	2002-10-25	2013-07-16	Paladin Labs Inc.	Controlled-release compositions
NZ539900A (en) *	2002-11-07	2008-03-28	Advanced Bionutrition Corp	Nutraceuticals and method of feeding aquatic animals
US6846497B2 (en) *	2003-01-30	2005-01-25	National Starch And Chemical Investment Holding Corporation	Rapidly expanding starches with altered crystalline structure
US20060172006A1 (en) *	2003-10-10	2006-08-03	Vincent Lenaerts	Sustained-release tramadol formulations with 24-hour clinical efficacy
EP1812025B1 (de)	2004-11-02	2012-09-05	Chr. Hansen A/S	Stabilisierte bakteriophagen-formulierungen
CA2491665A1 (fr) *	2004-12-24	2006-06-24	Louis Cartilier	Formulation de comprime pour liberation soutenue de principe actif
WO2007048219A2 (en)	2005-09-09	2007-05-03	Labopharm Inc.	Sustained drug release composition
PT1931346E (pt) *	2005-09-09	2012-08-14	Angelini Labopharm Llc	Composição de trazodona para administração uma vez por dia
JP5122436B2 (ja) *	2006-03-14	2013-01-16	国立大学法人奈良先端科学技術大学院大学	新規なヘパリン代替材料およびその製造方法
JP5453280B2 (ja) *	2007-10-16	2014-03-26	ラボファームインコーポレイテッド	アセトアミノフェンおよびトラマドールを持続的に放出するための二層組成物
US8563066B2 (en) *	2007-12-17	2013-10-22	New World Pharmaceuticals, Llc	Sustained release of nutrients in vivo
PT2234607E (pt)	2007-12-28	2011-09-30	Acraf	Formulação de libertação lenta com base numa associação de glicogénio e alginato
RS53866B1 (sr)	2008-07-16	2015-08-31	Richter Gedeon Nyrt.	Farmaceutske formulacije koje sadrže ligande dopaminskih receptora
CA2737247C (en) *	2008-09-15	2016-10-11	Labopharm Inc.	Starch-based microparticles for the release of agents disposed therein
SG196810A1 (en)	2009-01-23	2014-02-13	Acraf	Controlled release pharmaceutical or foodformulation and process for its preparation
US11274087B2 (en)	2016-07-08	2022-03-15	Richter Gedeon Nyrt.	Industrial process for the preparation of cariprazine
GB2567493B (en)	2017-10-13	2019-12-18	Altus Formulation Inc	Starch-based release modifying excipients and pharmaceutical compositions derived therefrom
US11547707B2 (en)	2019-04-10	2023-01-10	Richter Gedeon Nyrt.	Carbamoyl cyclohexane derivatives for treating autism spectrum disorder

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2987445A (en) *	1958-10-10	1961-06-06	Rohm & Haas	Drug composition
US3087860A (en) *	1958-12-19	1963-04-30	Abbott Lab	Method of prolonging release of drug from a precompressed solid carrier
US3622677A (en) *	1969-07-07	1971-11-23	Staley Mfg Co A E	Compressed tablets containing compacted starch as binder-disintegrant ingredient
US4369308A (en) *	1981-07-24	1983-01-18	National Starch And Chemical Corporation	Low swelling starches as tablet disintegrants
US4667590A (en) *	1984-12-10	1987-05-26	Mars, Inc.	Closed food processing system and liquid adjustment apparatus for use therein
CA2041774C (en) *	1990-11-27	1994-04-19	Mircea A. Mateescu	Use of cross-linked amylose as a matrix for the slow release of biologically active compounds
ATE137668T1 (de) *	1992-07-24	1996-05-15	Labopharm Inc	Vernetztes polyhydroxyl-material zur enzymatisch gesteuerten arzneistofffreisetzung

1997
- 1997-02-14 US US08/800,518 patent/US5807575A/en not_active Expired - Lifetime
1998
- 1998-02-10 AT AT98902905T patent/ATE212040T1/de not_active IP Right Cessation
- 1998-02-10 CA CA002280534A patent/CA2280534C/en not_active Expired - Fee Related
- 1998-02-10 DE DE69803159T patent/DE69803159T2/de not_active Expired - Lifetime
- 1998-02-10 PT PT98902905T patent/PT960131E/pt unknown
- 1998-02-10 WO PCT/CA1998/000106 patent/WO1998035992A1/en not_active Ceased
- 1998-02-10 AU AU59785/98A patent/AU726272B2/en not_active Ceased
- 1998-02-10 DK DK98902905T patent/DK0960131T3/da active
- 1998-02-10 NZ NZ337171A patent/NZ337171A/xx unknown
- 1998-02-10 ES ES98902905T patent/ES2171008T3/es not_active Expired - Lifetime
- 1998-02-10 IL IL13136998A patent/IL131369A/en not_active IP Right Cessation
- 1998-02-10 EP EP98902905A patent/EP0960131B1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
IL131369A0 (en)	2001-01-28
PT960131E (pt)	2002-06-28
US5807575A (en)	1998-09-15
NZ337171A (en)	2000-09-29
WO1998035992A1 (en)	1998-08-20
DE69803159D1 (de)	2002-02-21
CA2280534C (en)	2003-08-19
EP0960131A1 (de)	1999-12-01
AU5978598A (en)	1998-09-08
DE69803159T2 (de)	2002-08-29
ES2171008T3 (es)	2002-08-16
IL131369A (en)	2002-12-01
ATE212040T1 (de)	2002-02-15
DK0960131T3 (da)	2002-05-06
EP0960131B1 (de)	2002-01-16
CA2280534A1 (en)	1998-08-20

Legal Events

Date

Code

Title

Description

2001-03-01

FGA

Letters patent sealed or granted (standard patent)

2004-09-09

PC

Assignment registered

Owner name: LABOPHARM INC., LABOPHARM (BARBADOS) LIMITED, LABO

Free format text: FORMER OWNER WAS: LABOPHARM INC.

Publication	Publication Date	Title
AU726272B2 (en)	2000-11-02	Manufacture of cross-linked amylose useful as an excipient for control release of active compounds
EP1305009B1 (de)	2006-06-07	Quervernetzte stark amylose haltige stärke zur verwendung in pharmazeutischen formulierungen mit kontrollierter freisetzung und verfahren zu ihrer herstellung
US9101155B2 (en)	2015-08-11	Functional starch powder
AU2001271481A1 (en)	2002-04-11	Cross-linked high amylose starch for use in controlled-release pharmaceutical formulations and processes for its manufacture
US6616948B2 (en)	2003-09-09	Starch
JP4970839B2 (ja)	2012-07-11	押出し球状化医薬品ペレットにおける脱分岐でんぷんの使用
WO1999009066A1 (en)	1999-02-25	Preparation of pregelatinized high amylose starch and debranched starch useful as an excipient for controlled release of active agents
JP4306965B2 (ja)	2009-08-05	増量及び分解組成物、その達成方法及びその使用
EP1503738A1 (de)	2005-02-09	Verwendung von vollständig linearen kurzkettigen alpha-glukanen als pharmazeutischen hilfsstoff
US20070142325A1 (en)	2007-06-21	Starch
EP1325035B1 (de)	2008-05-28	Pharmazeutisch verwendbare Stärke und deren Herstellungsverfahren
JP4947613B2 (ja)	2012-06-06	造粒組成物の製造方法
Metta et al.	2022	A Review On: Disintegrants and Super Disintegrants with Prominence Role Of Starch As Disintegrant and its Methods of Modification
CN101024084B (zh)	2012-07-04	脱支淀粉在挤压-滚圆药丸中的用途
Szabo-Revesz et al.	2009	Potato starch in pharmaceutical technology-A review